Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 16, Problem 16.52P
Interpretation Introduction
Interpretation: The two different ways that can be used to prepare the given compound by Diels-Alder reaction is to be stated. The method that is preferred is to be explained.
Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
What kind of compounds are prepared using the Diels Alder reaction?
4
A possible side reaction is butadiene reacts with another butadiene via a Diels‐Alder reaction. Draw the structure of that product.
Chapter 16 Solutions
Organic Chemistry-Package(Custom)
Ch. 16 - Prob. 16.1PCh. 16 - Prob. 16.2PCh. 16 - Draw a second resonance structure for each...Ch. 16 - Prob. 16.4PCh. 16 - Prob. 16.5PCh. 16 - Prob. 16.6PCh. 16 - Prob. 16.7PCh. 16 - Determine the hybridization of the labeled atom in...Ch. 16 - Problem 16.10 Draw the structure consistent with...Ch. 16 - Problem 16.11 Neuroprotectin D1 (NPD1) is...
Ch. 16 - Problem 16.12 Using hybridization, predict how the...Ch. 16 - Problem 16.13 Use resonance theory to explain why...Ch. 16 - Prob. 16.13PCh. 16 - Prob. 16.14PCh. 16 - Prob. 16.15PCh. 16 - Problem 16.17 Draw a stepwise mechanism for the...Ch. 16 - Prob. 16.17PCh. 16 - Problem 16.19 Draw the product formed when each...Ch. 16 - Prob. 16.19PCh. 16 - Prob. 16.20PCh. 16 - Rank the following dienophiles in order of...Ch. 16 - Prob. 16.22PCh. 16 - Prob. 16.23PCh. 16 - Prob. 16.24PCh. 16 - Prob. 16.25PCh. 16 - Problem 16.27 Which compound in each pair absorbs...Ch. 16 - Prob. 16.27PCh. 16 - 16.29 Name each diene and state whether the...Ch. 16 - Prob. 16.29PCh. 16 - Prob. 16.30PCh. 16 - Prob. 16.31PCh. 16 - Prob. 16.32PCh. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - 16.35 Explain why the cyclopentadienide anion A...Ch. 16 - Explain each statement using resonance theory. a....Ch. 16 - 16.37 Draw the structure of each compound.
a. in...Ch. 16 - Draw and name all dienes of molecular formula...Ch. 16 - Prob. 16.39PCh. 16 - 16.39 Label each pair of compounds as...Ch. 16 - Prob. 16.41PCh. 16 - 16.41 Draw the products formed when each compound...Ch. 16 - Prob. 16.43PCh. 16 - 16.43 Treatment of alkenes A and B with gives the...Ch. 16 - 16.44 Draw a stepwise mechanism for the following...Ch. 16 - Prob. 16.46PCh. 16 - 16.46 Explain, with reference to the mechanism,...Ch. 16 - Prob. 16.48PCh. 16 - Prob. 16.49PCh. 16 - Prob. 16.50PCh. 16 - Prob. 16.51PCh. 16 - Prob. 16.52PCh. 16 - Prob. 16.53PCh. 16 - 16.53 Diels–Alder reaction of a monosubstituted...Ch. 16 - Prob. 16.55PCh. 16 - Prob. 16.56PCh. 16 - 16.55 Devise a stepwise synthesis of each compound...Ch. 16 - Prob. 16.58PCh. 16 - 16.57 A transannular Diels–Alder reaction is an...Ch. 16 - Draw a stepwise mechanism for the following...Ch. 16 - Draw the products of each reaction. Indicate the...Ch. 16 - Prob. 16.62PCh. 16 - Prob. 16.63PCh. 16 - Prob. 16.64PCh. 16 - 16.65 The treatment of isoprene with one...Ch. 16 - 16.66 The treatment of with forms B (molecular...Ch. 16 - Rank the following compounds in the order of...Ch. 16 - Prob. 16.68PCh. 16 - Prob. 16.69PCh. 16 - Prob. 16.70PCh. 16 - Prob. 16.71PCh. 16 - Prob. 16.72PCh. 16 - Prob. 16.73PCh. 16 - Prob. 16.74P
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Identify the reddish brown species obtained when the cyclopentadiene reacted withKOH. Why are the species and ferrocene aromatic?arrow_forwardWhich of the following will not act as diene reactant in a Diels Alder reaction? A) B) D) OCH3 H,CO Aarrow_forward2) Rank the following dienes in order of increasing rate of Diels-Alder reaction with maleic anhydride. You do not need to explain your ranking. H3C. H3CO Diene A Diene B Diene Carrow_forward
- Name and Draw the Phenolof all possible chemical (Electrophilic aromatic substitution) reactions of the compound namely; Halogenation (Chlorination or Bromination) Nitrationarrow_forwardChlordane, like DDT, is an alkyl halide that was used as an insecticide for crops such as corn and citrus and for lawns. In 1983, it was banned for all uses except against termites, and in 1988, it was banned for use against termites as well. Chlordane can be synthesized from two reactants in one step. One of the reactants is hexachlorocyclopentadiene. What is the other reactant?arrow_forwardWhat are the various synthesis of linear, branched, and/or cyclic ethers? Show reaction schemes, discuss reaction mechanisms step by step, and indicate any limitations or advantages of the approach.arrow_forward
- An organic compound A (C2H3N) is used as a solvent of choice for many organic reactions because it is not reactive in mild acidic and basic conditions. Compound A on treatment with Ni/ H2 forms B. When B is treated with nitrous acid at 273K ethanol is obtained. When B is warmed with chloroform and NaOH a foul smelling compound C formed. Identify A, B and C.arrow_forwardDraw the major products obtained from the reaction of one equivalent of HBr with the following compounds. For each reaction, indicate the kinetic product and the thermodynamic productarrow_forwardWhat is the major product formed from reacting cyclohexene in aqueous Br2, followed by treatment with potassium tert-butoxide?arrow_forward
- Draw the structure of each product from the reaction of benzene with 2-chloro-1-methylcyclohexane using AlCl 3 as the catalyst and Identify the major product.arrow_forwardDraw and discuss the mechanism (with arrows to show electron movements) of the Diels-Alder reaction between anthracene and maleic anhydride. Draw the orientation and phases of the reacting p-orbitals showing how they overlap in a “suprafacial” geometry to form productarrow_forwardDiphenylacetylene can be synthesized by the double dehydrohalogenation of 1,2-dibromo-1,2-diphenylethene. The sequence starting from (E)-1,2-diphenylethene consists of bromination to give the dibromide, followed by dehydrohalogenation to give a vinylic bromide, then a second dehydrohalogenation to give diphenylacetylene.(a) What is the structure, including stereochemistry, of the vinylic bromide?(b) If the sequence starts with (Z)-1,2-dibromo-1,2-diphenylethene, what is (are) the structure(s) of the intermediate dibromide(s)? What is the structure of the vinylic bromide?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning